Acetic Acid → HCID 536966, compound

HRID 463749Notes

Reaction equation

HRID 463749 reaction equation
[CH2:1]([CH:9]([C:13]([OH:15])=[O:14])C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]CC.[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.[OH-].[K+].[C:24](O)(=O)C.[CH:28]1[CH:33]=[CH:32]C=[CH:30][CH:29]=1>S(=O)(=O)(O)O.CCOCC>[CH2:19]([CH2:20][C:21]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:9][C:13]([O:15][CH3:24])=[O:14])=[O:16])[CH2:18][CH2:17][CH2:30][CH2:29][CH2:28][CH2:33][CH3:32]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 241BenzeneHCID 80803,4-dihydro-2H-pyranHCID 12972n-Octylmalonic acidHCID 14797Potassium Hydroxide

Product 1

HCID 536966HCID 536966, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

3 grams of the C8H17CH(CO2H)2 product obtained above were added, in small portions, to a mixture of 3.3 ml dihydropyran in 25 ml of benzene and 20 μl sulfuric acid, and stirred at 25° C., for 1 hour. Potassium hydroxide was added to neutralize the sulfuric acid, and the mixture was stirred for an additional 30 minutes. The solvent was then evaporated and, with 25 ml benzene, the mixture was added dropwise to NaH in 30 ml benzene, and stirred for 1 hour. 3 g of the CH3OCO(CH2)7COCl product prepared above was added dropwise and the mixture stirred overnight. Acetic acid (0.3 ml) was added and the mixture refluxed for 4 hours. The residue was taken up in ether, washed with 1N NaOH, water and brine, and dried. Chromatography on silica gel with 15% ethylacetate and hexane gave 1.5 g of C8H17CH2CO(CH2)7COOCH3.

Workup

  1. stirringthe mixture was stirred for an additional 30 minutes
  2. customThe solvent was then evaporated and, with 25 ml benzene
  3. additionthe mixture was added dropwise to NaH in 30 ml benzene
  4. stirringstirred for 1 hour
  5. custom3 g of the CH3OCO(CH2)7COCl product prepared
  6. additionabove was added dropwise
  7. stirringthe mixture stirred overnight
  8. temperaturethe mixture refluxed for 4 hours
  9. washwashed with 1N NaOH, water and brine
  10. customdried

Sources & evidence

ORD record
ord-db5ab25215ea4ab5a8de7ad288927867
Source dataset
uspto-grants-1985_10
Patent number
US04544668

Reaction notes

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